Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile

In the crystal, O—H⋯O, C—H⋯O, and C—H⋯N hydrogen bonds connect molecules, generating molecular layers parallel to (100). These layers are linked together by weak C—H⋯π interactions and van der Waals forces.


Chemical context
Functionalized derivatives of carbo-and heterocyclic compounds are of great interest in the fields of organic synthesis, catalysis, materials science and medicinal chemistry (Zubkov et al., 2018;Shikhaliyev et al., 2019;Viswanathan et al., 2019;Gurbanov et al., 2020;Khalilov et al., 2021). In particular, -dicarbonyl compounds are important chemical substrates for the construction of various classes of organic compounds (Kaur et al., 2021).

Hirshfeld surface analysis
A Hirshfeld surface for the title compound and its associated two-dimensional fingerprint plots were analyzed and calculated using CrystalExplorer (Version 17.5; Turner et al., 2017). Hirshfeld surfaces allow for the display of intermolecular interactions by using distinct colours and intensities to indicate short and long contacts, as well as the relative strengths of the interactions. The three-dimensional (3D) Hirshfeld surface of the title compound plotted over d norm in the range from À0.5877 to +1.7202 a.u. is shown in Fig. 6. As discussed above, the O3-H3Á Á ÁO1 interactions play a key role in the molecular packing of the title compound.
In the crystal of UPOMOE, the central cyclohexane ring adopts a chair conformation. Molecules are linked by N-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds, forming layers parallel to (100), which interact via the van der Waals forces between them.
In the crystal of MEHMOC01, the molecules are linked into complex sheets by two C-HÁ Á ÁO hydrogen bonds and three C-HÁ Á ÁN hydrogen bonds.
In the crystal of SODHAW, molecules are linked via pairs of O-HÁ Á ÁN hydrogen bonds, forming inversion dimers. The dimers are linked via C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, forming chains parallel to [001]. C-HÁ Á ÁF hydrogen bonds link the chains into sheets lying parallel to (100).

Synthesis and crystallization
To a solution of 2-(3-phenylallylidene)malononitrile (0.92 g, 5 mmol) and benzoylacetone (1.68 g, 10 mmol) in benzene (25 ml), 3-4 drops of 1-methylpiperazine were added and the mixture was stirred for 10 min and kept at room temperature   for 72 h. Benzene (15 ml) was then removed from the reaction mixture by distillation, which was left overnight. The crystals which formed were separated by filtration and recrystallized from an ethanol-water (1:1 v/v) solution (yield 41%; m.p. 514-515 K).

Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 3. Due to large differences between calculated and observed intensities, about 40 reflections were omitted from the refinement. The H atom of the OH group was located in a difference map and its positional parameters were allowed to refine freely [O3-H3 = 0.93 (3) Å ], with U iso (H) = 1.5U eq (O). All H atoms bound to C atoms were positioned geometrically and refined as riding, with C-H = 0.95 (aromatic), 0.99 (methylene), 1.00 (methine) and 0.98 Å (methyl), with U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for the others.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.